CAS: 214766-78-6; Degarelix

该化合物是一种合成激素,是一种主要用于治疗前列腺癌的合成激素激素(GnRH)对抗剂,主要用于治疗前列腺癌,其作用是抑制释放润滑荷尔蒙(LH)和刺激激素(FSH),导致睾丸素水平迅速下降.这一机制有助于减少前列腺癌细胞的刺激作用,这些细胞往往依靠睾丸酮来生长.Degarelix的特征是,它能够提供与传统的GnRH刺激剂(GnRH)相比的快速行动启动能力,该激素水平最初会提高,然后导致下降.该物质通常通过亚乳性注射来施用,并因其相对有利的副作用而闻名.尽管它仍然可能引起诸如注射点疼痛,热闪光和重量增殖等反应.它的化学结构包括一系列氨酸,有助于其生物活动,并且被归类为一种浸泡药物.与任何药物一样,它的使用应当由保健专业人员监测,以管理潜在效果和确保功效.

英文名称Degarelix
中文名称醋酸地加瑞克
IUPAC名称(S)-N-(4-((2S,5S,8R,11R,14R)-2-(((R)-1-(((S)-1-(((S)-1-((S)-2-(((R)-1-amino-1-oxopropan-2-yl)carbamoyl)pyrrolidin-1-yl)-6-(isopropylamino)-1-oxohexan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-(4-ureidophenyl)propan-2-yl)carbamoyl)-11-(4-chlorobenzyl)-5-(hydroxymethyl)-14-(naphthalen-2-ylmethyl)-4,7,10,13,16-pentaoxo-8-(pyridin-3-ylmethyl)-3,6,9,12,15-pentaazaheptadecyl)phenyl)-2,6-dioxohexahydropyrimidine-4-carboxamide
其它别名DEGARELIX; Degarelix acetate; N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-4-[2,6-dioxohexahydropyrimidin-4(S)-ylcarboxamido]-L-phenylalanyl-4-ureido-D-phenylalanyl-L-leucyl-N6-isopropyl-L-lysyl-L-prolyl-D-alaninamide acetate; D-Alaninamide, N-acetyl-3-(naphtalen-2-yl)-D-alanyl-4-chloro-D-phenylalanyl-3-(pyridin-3-yl)-D-alanyl-L-seryl-4-((((4S)-2,6-dioxohexahydropyrimidin-4-yl)carbonyl)amino)-L-phenylalanyl-4-(carbamoylamino)-D-phenylalanyl-L-leucyl-N6-(1-methylethyl)-L-lysyl-L-prolyl-
CAS编号214766-78-6
MFCD编号:MFCD05860888
EINECS号:807-277-4
FDA UNII编号:SX0XJI3A11
分子式:C82H103ClN18O16
分子量:1632.26
产品CID: 1116354
同类组份化合物CAS214766-78-6 (free base)934246-14-7 (acetate)
产品分类生物化工 → 多肽

相似结构搜索
InChIKey: MEUCPCLKGZSHTA-XYAYPHGZSA-N
MEUCPCLKGZSHTA-XYAYPHGZSA-N…
计算化学: 氢键受体数18.0氢键供体数17.0可旋转键数41.0

物理性质

密度1.3±0.1 g/cm3
pKa:10.38±0.40(预测)
PSA:512.87
LogP:4.45
折射率1.620
溶解性DMSO:10.0(Max Conc. mg/mL);6.13(Max Conc. Mm) 水:25.0(Max Conc. mg/mL);15.32(Max Conc. Mm)
外观形态白色至类白色固体
储存条件请置于阴暗处, 惰性气氛中,冷冻保存, 低于 -20°C
产品应用该化合物是一种基于荷尔蒙的化疗, 可以治疗前列腺癌.

欧盟法规

C&L通报

上下游产品

Fm°C-Ser(tBu)-OH acetic anhydride N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(pyridin-3-yl)propanoic acid

合成工艺路线路线简述

79990-15-1 + 71989-33-8 + 138774-94-4 + 35661-60-0 + 175453-08-4 + 201003-48-7 + 1433975-21-3 + 1253282-31-3 + 71989-31-6 + 142994-45-4 = 214766-78-6
反应条件:1.1 Reagents: Pyrrolidine Solvents: Dimethylformamide1.2 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.3 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.4 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.5 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.6 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.7 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.8 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.9 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.10 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.11 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.12 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.13 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.14 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.15 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.16 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.17 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.18 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.19 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.20 Reagents: Diisopropylcarbodiimide,1-Hydroxybenzotriazole Solvents: Dimethylformamide; 1 H,25 +/- 5 °C1.21 Reagents: Pyrrolidine Solvents: Dimethylformamide; 15 Min,Rt1.22 Reagents: Diisopropylethylamine Solvents: Dimethylformamide; 30 Min,Rt1.23 Reagents: Trifluoroacetic Acid; 0.5 - 40 H,25 +/- 5 °C
标题:Improved Process For Production Of Degarelix Acetate
参考文献:India]

79990-15-1 + 71989-33-8 + 35661-60-0 + 142994-19-2 + 201003-48-7 + 1253282-31-3 + 324017-22-3 + 71989-31-6 + 142994-45-4 + 37440-01-0 = 214766-78-6
反应条件:1.1 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.2 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.3 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.4 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.5 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.6 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.7 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.8 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.9 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.10 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.11 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.12 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.13 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.14 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.15 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.16 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.17 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.18 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.19 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.20 Reagents: Piperidine Solvents: Dimethylformamide; 30 Min1.21 Reagents: Diisopropylcarbodiimide,Ethyl 2-Cyano-2-(Hydroxyimino)Acetate Solvents: Dimethylformamide; 20 Min,0 - 10 °C; 1 - 4 H,0 - 20 °C1.22 Reagents: Trifluoroacetic Acid Solvents: Water; 2.5 H,Rt
标题:Process For Preparation Of Degarelix
参考文献:China]

79990-15-1 + 71989-33-8 + 138774-94-4 + 35661-60-0 + 142994-19-2 + 201003-48-7 + 71989-31-6 + 5988-19-2 + 142994-45-4 + 1118-02-1 = 214766-78-6
反应条件:1.1 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.2 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.3 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.4 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.5 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.6 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.7 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.8 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.9 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.10 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.11 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.12 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.13 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.14 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.15 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.16 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.17 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.18 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.19 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.20 Reagents: Piperidine Solvents: Dimethylformamide; 10 Min,Rt1.21 Solvents: Dimethylformamide,Pyridine; Cooled; 2 H,25 - 35 °C1.22 Reagents: Hydrazine Hydrate (1:1) Solvents: Dimethylformamide; 10 Min,Rt1.23 Solvents: Dimethylformamide; Cooled; 2 H,Cooled; 24 H,25 - 35 °C1.24 Reagents: Tetrabutylammonium Fluoride Solvents: Dimethylformamide; 2 H,25 - 35 °C1.25 Reagents: Diisopropylcarbodiimide,6-Chloro-1-Hydroxybenzotriazole Solvents: Dimethylformamide; 0 - 10 °C; 2 H,25 - 35 °C1.26 Solvents: Water; Rt
标题:Process For Preparation Of Degarelix Acetate
参考文献:China

在三异丙基硅烷,三氟乙酸体系中,用水用作溶剂,化学反应 2.0H,反应生成醋酸地加瑞克
参考文献:Ajiphase®:一种高效的合成方法,通过fmoc策略在溶液阶段延伸一锅肽
标题:Ajiphase®:一种高效的合成方法,通过fmoc策略在溶液阶段延伸一锅肽
摘要:我们先前报道了一种有效的肽合成方法ajiphase®,该方法包括重复的反应和通过沉淀分离.该方法利用具有长链烷基的锚分子作为c末端的保护基.为了进一步改进该方法,我们开发了一种肽序列的一锅法合成方法,其中合成中间体通过溶剂萃取而不是沉淀法进行分离.在新工艺中使用了支链锚分子,与以前的方法相比,该方法显着提高了长肽的溶解度和操作效率,而以前的方法采用沉淀法进行分离和使用直链脂族基团.这种基于溶剂萃取的策略的另一个先决条件是使用硫代苹果酸和dbu进行fmoc脱保护,
Doi:10.1002/anie.201702931

海关参考信息

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2902902000-精萘
2903919090-氯苯
2905121000-正丙醇
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专利信息

专利号:US-12351573-B2
优先权日:2019-05-09
标题:Compounds for use in synthesis of peptidomimetics
发明人：AL-ABED YOUSEF; CHENG KAI FAN
权利人:FEINSTEIN INSTITUTES FOR MEDICAL RESEARCH
摘要:Synthesis of O-benzotriazole and O-imidazole synthons are described. Uses of synthons in synthesis of azapeptides and other peptidomimetics, azapeptides and other peptidomimetics synthesized from the synthons and uses of azapeptides and other peptidomimetics are also described.

专利号:US-2023159450-A1
优先权日:2020-05-08
标题 :Dimers for use in synthesis of peptidomimetics
发明人：AL-ABED YOUSEF; ALTITI AHMAD
权利人:FEINSTEIN INSTITUTES FOR MEDICAL RESEARCH
摘要:Dimers for use in synthesis of peptidomimetics are described. Uses of dimers as synthons in synthesis of azapeptides and other peptidomimetics, azapeptides and other peptidomimetics synthesized from the dimers and uses of azapeptides and other peptidomimetics are also described.

专利号:US-2020354404-A1
优先权日:2019-05-09
标题 :Peptidomimetic agents, synthesis and uses thereof
发明人：AL-ABED YOUSEF
权利人:FEINSTEIN INSTITUTES FOR MEDICAL RESEARCH
摘要:Compounds for use in synthesis of peptidomimetic agents; synthesis of peptidomimetic agents; peptidomimetic diagnostic and therapeutic agents; and uses of the compounds and peptidomimetic agents in drug discovery, diagnosis, prevention and treatment of diseases are described.

专利号:US-2017283878-A1
优先权日:2015-12-11
标题:Modulation of globoseries glycosphingolipid synthesis and cancer biomarkers
发明人：WONG CHI-HUEY; WU CHUNG-YI; CHEUNG SARAH K C; CHUANG PO-KAI; HSU TSUI-LING
权利人:ACADEMIA SINICA
摘要:The present disclosure relates to methods and compositions which can modulate the globoseries glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globoseries glycosphingolipid SSEA-3/SSEA-4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta-4GalNAcT-I; or beta-3GalT-V enzymes in the globoseries synthetic pathway. Additionally, the present disclosure is also directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA-3/SSEA-4/GLOBO H associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globoseries glycosphingolipid synthesis. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions. Furthermore, the instant disclosure also relates to cancer stem cell biomarkers for diagnostic and therapeutic uses.

专利号:WO-2019202613-A1
优先权日:2018-04-20
标题 :Improved process for production of degarelix acetate
发明人：ALAPARTHI LAKSHMI PRASAD; RAO GINJUPALLI SADASIVA; CHOWDARY TALLURI BHUSHAIAH; MANTRI ANAND VIJAYKUMAR; DHARMESH MAHENDRABHAI SHAH; MEHTA TUSHAR BHARATKUMAR
权利人:ALAPARTHI LAKSHMI PRASAD
摘要:: The present invention relates to improved manufacturing process for preparing Degarelix Acetate using method of deprotection in solid phase peptide synthesis in which the improvement comprises: treating with Pyrrolidine in Dimethylformamide in small volume. Also disclosed is degarelix of high purity prepared by the method of the invention and the use of Fmoc and deprotection with Pyrrolidine in small volume in the synthesis of degarelix.

专利号:US-11649285-B2
优先权日:2016-08-03
标题 :Identification of VSIG3/VISTA as a novel immune checkpoint and use thereof for immunotherapy
发明人：KALABOKIS VASSILIOS; WANG JINGHUA; WU GUOPING; BAZAN JOSE FERNANDO; VALLEY CHRISTOPHER CARLIN
权利人:BIO TECHNE CORP
摘要:The ligand for VISTA is identified (VSIG3) as well as the use of this ligand and receptor interaction in the identification or synthesis of a VSIG3 agonist or antagonist compounds, preferably antibodies, polypeptides and fusion proteins which agonize or antagonize the effects of VSIG3 and/or VISTA and/or the VSIG3/VISTA interaction. These antagonists may be used to suppress VSIG3/VISTA's suppressive effects on T cell immunity, and more particularly used in the treatment of cancer, or infectious disease. These agonist compounds may be used to potentiate or enhance VSIG3/VISTA's suppressive effects on T cell immunity and thereby suppress T cell immunity, such as in the treatment of autoimmunity, allergy or inflammatory conditions. Screening assays for identifying these agonists and antagonist compounds are also provided.

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主要参考文献

1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Degarelix. 2023 May 28. 8(8):CD012548. doi: 10.1002/14651858.CD012548.pub2.
3: Devos G, Tosco L, Baldewijns M, Gevaert T, Goffin K, Petit V, Mai C, Laenen A, Raskin Y, Van Haute C, Goeman L, De Meerleer G, Berghen C, Devlies W, Claessens F, Van Poppel H, Everaerts W, Joniau S. ARNEO: A Randomized Phase II Trial of Neoadjuvant Degarelix with or Without Apalutamide Prior to Radical Prostatectomy for High-risk Prostate Cancer. Eur Urol. 2023 Jun;83(6):508-518. doi: 10.1016/j.eururo.2022.09.009. Epub 2022 Sep 24. PRONOUNCE Study Investigators. Cardiovascular Safety of Degarelix Versus Leuprolide in Patients With Prostate Cancer: The Primary Results of the PRONOUNCE Randomized Trial. Circulation. 2021 Oct 19;144(16):1295-1307. doi: 10.1161/CIRCULATIONAHA.121.056810. Epub 2021 Aug 30. Erratum in: Circulation. 2021 Oct 19;144(16):e273.
5: Sari Motlagh R, Abufaraj M, Mori K, Aydh A, Rajwa P, Katayama S, Grossmann NC, Laukhtina E, Mostafai H, Pradere B, Quhal F, Karakiewicz PI, Enikeev DV, Shariat SF. The Efficacy and Safety of Relugolix Compared with Degarelix in Advanced Prostate Cancer Patients: A Network Meta-analysis of Randomized Trials. Eur Urol Oncol. 2022 Apr;5(2):138-145. doi: 10.1016/j.euo.2021.07.002. Epub 2021 Jul 21. 34(10):423-6. doi: 10.1016/j.urolonc.2016.05.029. Epub 2016 Jun 28. 18(6):851-60. doi: 10.1517/13543780902954713. 74(6):699-712. doi: 10.1007/s40265-014-0211-y. 31 Pt

合成参考文献

合成方法参考DOI号:10.1021/acs.oprd.9b00540

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